My main music player is iTunes as I am a apple man
So issues I had was the music is all in .m4a and I wanted a quick easy way to get the music to a USB stick. So my steps are now.
<ul>[*]I have a playlist in iTunes with all music I want on it[*]I have notpod which syncs the playlist to the USB in the desired way i.e. not pod allows you to set folder structure with different options I have settled with Album - Artist/Track[*]Then I use Free m4a to mp3 converter and point it at the usb and away it goes remembering to set it to delete from source so I end up with MP3s.[*]plug USB in I currently have 1.2 days worth of music on it.[/list]The only issue is when you want to add more music but all you do is delete all music of the usb and start the process again.
I also upgraded the software of the media nav with music on with no issues once complete I just deleted all the files and folders on the usb that weren't music.
USB Structure
\\My Name\Album - Artist\Track
Hope this helps other people out there